I think this is a good question. I echo the previous comments, but would add that First Aid for Step 2 CS is a great resource for this type of thing. You wont probably use it till you prep for the CS exam, but it has a bunch of bread-and-butter cases with appropriate HPI/ROS questions and differential dxes and workups. I think after using this book and memorizing (and understanding) the differentials of the most common presenting complaints (e.g. chest pain, cough, joint pain, etc.) you can quickly master this very important skill.
I think while you go through all of this you'll start to realize that some of the most basic chief complaints can be caused by many different organ systems. This is why in general its a good idea to always start out doing a complete ROS for every patient you see. An easy way to remember this is to think by system (e.g. urinary sxs, GI sxs, resp sxs, constitutional sxs, etc.). This is b/c especially as a student you wont necessarily know the differential when a patient presents to you right away, so its best to ask everything and then later look things up. Also this prevents you from having to go back multiple times to the patient b/c you forgot to ask them a question, this could be very annoying for the patient.
I also think its interesting that medical school (at least in the first two years) dont really focus on this skill. Instead its all about memorizing the features of all the different disease entities you may encounter (but likely wont ever see). Yes, 3rd year is all about acquiring this skill, but it can be intimidating when you've learned medicine one way and now have to all of a sudden start over and learn a different way.
